Walk through the sights and sounds of Old San Juan

Delve into Local Strolls, a series where writers reveal their favorite walks in cities they love. Each route offers a snapshot of urban life, guiding you to lesser-known attractions and cherished local spots. Here, Jackie Gutierrez-Jones takes us on a gentle stroll through the historic landmarks, cafes, and shops of Old San Juan. 

San Juan is a delightful mix of two different worlds living in cacophonous harmony. Its origins date back to 1521, so it isn’t uncommon to find historical colonial buildings and artifacts butting up against the trappings of modern city life.

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There are two ways to take in the colorful sights and Caribbean rhythms floating up from the waterfront expanse and squares – the coastal route, which takes you around the island's shores, and the interior streets, where I like to dive into locally run restaurants for a snack and do some shopping. 

You can explore both separately, or you can embark on my favorite route; a combination of the best historical and cultural stops in one hour-long stroll. 

Don’t be surprised if you’re joined by a gaggle of cruise travelers at the get-go – it starts just west of the port. But this is where San Juan’s history really comes to life, and it starts at the Paseo de la Princesa, a charming tree-lined esplanade with pristine views of San Juan Bay. 

Artists and street vendors are hawking their wares alongside flocks of pigeons and doves that roam the nearby Parque de las Palomas. The birds, incidentally, are quite bold and lost their wariness of people long ago – I keep any food closely under wraps here.

About four minutes northwest, there’s La Fortaleza, a stony fortress and military stronghold that was built in 1533. The governor lives here now, and it’s always fun to think I might catch a glimpse of them going about their business.  

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From there, go north past the Casa Blanca – the intended residence for Puerto Rico’s first governor Juan Ponce de Leon, and the de Leon family’s ancestral home – until you reach Castillo San Felipe del Morro, a six-level fortress with a cannon. 

Here’s where I like to take a quick 15-20 minute break on the rolling green lawn surrounding the site. The expansive view of the bay is a dreamy backdrop as groups of families and friends picnic and fly kites on a breezy day. It’s a great place to recharge the batteries a bit and do some people-watching before heading on your way. 

After catching your breath, you’ll walk southeast on Calle Norzagaray. I like to take my time here, not only because the street gets quite steep at some points, but because there are plenty of forts, cafes and shops in the surrounding areas to pop into for a quick detour or refreshment. 

The busy Saturday farmer’s market at the Museo de San Juan and the amazing ocean views at the Bastion de San Sebastian are worth spending some extra time on.  I also really love stopping into Bien Papayas near the Castillo de San Cristobal for tropical juice or the eponymous smoothie with papaya, vanilla, brown sugar and milk.

Castillo de San Cristóbal, a UNESCO World Heritage site, is a four-minute walk from Bien Papayas and one of the biggest forts on the island. 

It was constructed to defend Old San Juan against land attacks from the east via Puerta de Tierra, and its 150-foot walls remain. If this is your first time in the city, it’s worth paying the entrance fee and taking one of the hour-long guided tours they offer to check out the barracks and dungeons – a cool (albeit kind of morbid) respite from the tropical heat.   

After passing by (or exploring) Castillo de San Cristóbal, you’ll walk through Plaza de Colón with its statue of Christopher Columbus and adorable outdoor cafes on your way to the Calle de la Fortaleza. 

This road cuts a swath through Old San Juan, and is filled with jewelry stores, perfumeries, clothing boutiques, and restaurants. Finish up your stroll with a pic under the Instagram-famous umbrella canopy near the actual Fortaleza. 

The colors of the umbrellas change throughout the year, which I think is a perfectly fine excuse to return to the island and go on another paseo.

From this point, you can walk back to the Paseo de la Princesa and make your way to the port as the cruise passengers board their ships at the end of the day. I like watching the giant cruise liners gently navigate their way back into the ocean before the sun sets on the horizon.  

Distance: approx 3.8km

Time: approx 55 minutes